63317-99-7

Basic information

• Product Name: 5,9-hexadecadienoic acid
• Synonyms: 5,9-hexadecadienoic acid
• CAS NO: 63317-99-7
• Molecular Formula: C16H28 O2
• Molecular Weight: 252.39
• Mol File: 63317-99-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 346.6°C at 760 mmHg
• Flash Point: 243.6°C
• Appearance: /
• Density: 0.919g/cm³
• Vapor Pressure: 1E-05mmHg at 25°C
• Refractive Index: 1.479
• CAS DataBase Reference: 5,9-hexadecadienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5,9-hexadecadienoic acid(63317-99-7)
• EPA Substance Registry System: 5,9-hexadecadienoic acid(63317-99-7)

Safety Data

• Hazardous Substances Data: 63317-99-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8,11-12H,2-6,9-10,13-15H2,1H3,(H,17,18)/b8-7+,12-11+

Upstream product

• 1448312-51-3 2-(hexadeca-5Z,9Z-dien-1-yloxy)tetrahydro-2H-pyrane 
• 22433-33-6 Nona-1,2-dien 
• 910095-87-3 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran 
• 475207-21-7 1-(tert-butyldimethylsilyloxy)-5,9-hexadecadiyne 
• 475207-23-9 5,9-hexadecadiyn-1-ol 
• 475207-24-0 5,9-hexadecadiynal 
• 628-16-0 hexa-1,5-diyne 
• 91647-85-7 1,5-dodecadiyne 
• 475207-22-8 5,9-hexadecadiynoic acid 
• 250786-06-2 2-(3-undecynyl)-1,3-dioxolane 
• 250786-07-3 (Z)-2-(dec-3-en-1-yl)-1,3-dioxolane 
• 629-05-0 n-octyne 
• 68820-32-6 (Z)-4-undecenal 
• 17857-14-6 (3-carboxypropyl)(triphenyl)phosphonium bromide 

Relevant articles and documents

Total synthesis and biological evaluation of (5Z,9Z)-5,9-hexadecadienoic acid, an inhibitor of human topoisomerase I

The naturally occurring (5Z,9Z)-5,9-hexadecadienoic acid was synthesized stereochemically pure in six steps starting with commercially available 1,5-hexadiyne. The title compound was antimicrobial against the Gram-positive bacteria Staphylococcus aureus (MIC 80 μM) and Streptococcus faecalis (MIC 200 μM), but inactive against Gram-negative bacteria such as Pseudomonas aeruginosa. In addition, the (5Z,9Z)-5,9-hexadecadienoic acid completely inhibits human topoisomerase I at a concentration of 800 μM, while 5,9-hexadecadiynoic acid and hexadecanoic acid do not inhibit topoisomerase I (>1000 μM). This comparison reveals that the cis double bond geometry in the title compound is required for topoisomerase I inhibition. Moreover, these results suggest that the antimicrobial activity of (5Z,9Z)-5,9-hexadecadienoic acid against either S. aureus or S. faecalis could be a result, at least in part, of the inhibitory activity of the acid against topoisomerases.

Facile syntheses for (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid through a common synthetic route

The Δ5,9 fatty acids (5Z,9Z)-5,9-hexadecadienoic acid, (5Z,9Z)-5,9-nonadecadienoic acid, and (5Z,9Z)-5,9-eicosadienoic acid were synthesized for the first time in four steps (9-12% overall yield) starting from commercially available 2-(2-bromoethyl)-1,3-dioxolane. The synthetic approach provided enough material to corroborate the structure and stereochemistry of (5Z,9Z)-5,9-nonadecadienoic acid which was recently identified in the flowers of Malvaviscus arboreus (Malvaceae). The novel phospholipids 1-hexadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine and 1-octadecanoyl-2-[(5Z,9Z)-5,9-eicosadienoyl]-sn-glycero-3-phosphocholine were also synthesized from commercially available L-α-phosphatidylcholine (egg yolk) and characterized by positive ion electrospray mass spectrometry. These are the first examples of unsymmetrical phospholipids with saturated fatty acids at the sn-1 position and Δ5,9 fatty acids at the sn-2 position. Copyright (C) 1999 Elsevier Science Ireland Ltd.